US3984392A - Liquid crystalline azobenzene compounds - Google Patents

Liquid crystalline azobenzene compounds Download PDF

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Publication number
US3984392A
US3984392A US05/531,087 US53108774A US3984392A US 3984392 A US3984392 A US 3984392A US 53108774 A US53108774 A US 53108774A US 3984392 A US3984392 A US 3984392A
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US
United States
Prior art keywords
compounds
liquid crystalline
mol
sub
glass plate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US05/531,087
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English (en)
Inventor
Jan van der Veen
Theodorus Cornelis Jozef Maria Hegge
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US Philips Corp
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US Philips Corp
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Publication date
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Priority to US05/707,530 priority Critical patent/US4097120A/en
Application granted granted Critical
Publication of US3984392A publication Critical patent/US3984392A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds

Definitions

  • the invention relates to novel liquid crystalline compounds.
  • liquid crystalline compounds have too high a melting point or too small a liquid-crystalline temperature range for practical applications.
  • n has the value 6 or 7, and mixtures of said compounds meet the object in view.
  • the compounds are resistant to the effects of temperature, light and hydrolysis. They exhibit no dynamic scattering.
  • the compounds can be applied as solvents in E.S.R. and N.M.R.-spectrocopy. Furthermore, they may be employed in displays. If desired they may be mixed with other liquid crystalline compounds, for example nematic liquid crystalline compounds which exhibit dynamic scattering. Examples of nematic liquid crystalline compounds which may be mixed with the compounds according to the invention are the compounds described in French Pat. No. 1,537,000, the published Netherlands Pat. application No. 7,007,912, and the published German Pat. applications 1,928,242; 2,017,727 and 2,038,780.
  • the invention relates to novel compounds of the formula ##SPC2##
  • n 6 or 7, and to mixtures which contain at least one of said compounds.
  • the azo-compound which corresponds to said compound, p-n.butyl-o'-hydroxy-p'-methoxyazobenzene even appears to melt at a still higher temperature, 68°C, and to be liquid crystalline in undercooled condition only, to 60°C.
  • the compounds of the formula 1 can be obtained in accordance with methods known per se.
  • the compounds may be prepared by reacting o, p-dihydroxy-p'-butylazobenzene or an alkali metal salt thereof with an alkylhalide of the formula 2
  • n 6 or 7 and X represents an iodine or bromine atom.
  • the reaction is preferably performed in a highly polar aprotic solvent, such as for example dimethylformamide, at temperatures between room temperature and the boiling point of the mixture.
  • the azobenzene compound which is the starting point of said reaction is obtained by reacting p-butylphenyl-diazonium-tetra-fluoroborate with resorcinol in acetone/water between 0° and 5°C.
  • the invention also relates to a display cell provided with at least two electrodes and a nematic liquid crystalline material disposed therebetween, characterized in that the liquid crystalline material contains at least one or more of the compounds of the formula 1.
  • FIG. 1 shows a plan view of the display cell before the polarization filters were mounted
  • FIG. 2 is a cross-section taken at the line A-B after the filters were mounted.
  • the diazoniumborofluoride was dissolved in a mixture of 100 ml of water and acetone (1 : 1). Subsequently 0.15 mol of resorcinol, solved in 120 ml of water, were added. Said solution was kept in the refrigerator for 16 hours and subsequently poured into 500 ml of water. The resultant precipitate of 4-n-butyl-2', 4'-dihydroxyazobenzene was filtered off.
  • connection points 8 which consisted of indium oxide, as well as on the part of glass plate 3 which extended beyond the glass plate 1.
  • the underside of glass plate 1 and the upper side of glass plate 3 were provided with polarising filters.
  • the direction of polarization of the two filters was parallel to the direction in which plate 1 had been rubbed with lens paper.
  • the display cell thus obtained when viewed through showed a dark image field.
  • the molecules of the nematic liquid crystalline substance are disposed parallel to the surface and in the direction of rubbing. Since said directions are perpendicular to each other, the liquid crystalline layer has a twisted structure.
  • FIG. 1 shows a plan view of the display cell before the polarisation filters were mounted
  • FIG. 2 is a cross-section taken at the line A-B after the filters were mounted.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)
US05/531,087 1973-12-13 1974-12-09 Liquid crystalline azobenzene compounds Expired - Lifetime US3984392A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US05/707,530 US4097120A (en) 1973-12-13 1976-07-22 Liquid crystalline compounds and mixtures

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NLAANVRAGE7317074,A NL174720C (nl) 1973-12-13 1973-12-13 Beeldweergeefcel en methode voor de vervaardiging van een vloeibaar kristallijn p-n.butyl-p'-alkoxyazobenzeen.
NL7317074 1973-12-13

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US05/707,530 Division US4097120A (en) 1973-12-13 1976-07-22 Liquid crystalline compounds and mixtures

Publications (1)

Publication Number Publication Date
US3984392A true US3984392A (en) 1976-10-05

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US05/531,087 Expired - Lifetime US3984392A (en) 1973-12-13 1974-12-09 Liquid crystalline azobenzene compounds

Country Status (10)

Country Link
US (1) US3984392A (enrdf_load_stackoverflow)
JP (2) JPS598270B2 (enrdf_load_stackoverflow)
BE (1) BE823358A (enrdf_load_stackoverflow)
CH (1) CH612415A5 (enrdf_load_stackoverflow)
DE (1) DE2456804C2 (enrdf_load_stackoverflow)
FR (1) FR2254556B1 (enrdf_load_stackoverflow)
GB (1) GB1435269A (enrdf_load_stackoverflow)
IT (1) IT1027046B (enrdf_load_stackoverflow)
NL (1) NL174720C (enrdf_load_stackoverflow)
SE (1) SE416199B (enrdf_load_stackoverflow)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4134888A (en) * 1975-12-22 1979-01-16 Rca Corporation Cholesteryl carbonates and carbamates of azo dyes
US4199503A (en) * 1977-10-12 1980-04-22 Basf Aktiengesellschaft Phenylazophenyloxytriazolyl compounds
US5314997A (en) * 1991-07-11 1994-05-24 Ricoh Company, Ltd. Optically active azo compound, producing method thereof, and liquid crystal composition containing said compound
US20040105896A1 (en) * 1997-09-19 2004-06-03 Crosfield Limited Metal compunds, mixed or sulphated, as phosphate binders
US20090317459A1 (en) * 2006-01-31 2009-12-24 Ineos Healthcare Limited Material
US20100203152A1 (en) * 2007-07-27 2010-08-12 Ineos Healthcare Kimited Mixed metal compounds used as antacids
US20100215770A1 (en) * 2007-10-16 2010-08-26 Maurice Sydney Newton Mixed metal compounds for treatment of hyperphosphataemia
US9066917B2 (en) 2009-08-03 2015-06-30 Cytochroma Development Inc. Mixed metal compound
US9566302B2 (en) 2010-02-04 2017-02-14 Opko Ireland Global Holdings, Ltd. Composition comprising mixed metal compounds and xanthan gum

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4979805A (en) * 1984-07-23 1990-12-25 Canon Kabushiki Kaisha Ferroelectric liquid crystal device containing optically active azo or azoxy benzene type mesomorphic compound with extended life

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2024269A1 (en) * 1970-05-19 1971-12-02 Merck Patent Gmbh Nematic mixtures - of low melting point, used in electronics
US3773747A (en) * 1970-03-28 1973-11-20 Merck Patent Gmbh Substituted azoxy benzene compounds
US3853785A (en) * 1971-10-14 1974-12-10 Univ Temple Stable liquid crystal mixtures including anil-type nematic compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3773747A (en) * 1970-03-28 1973-11-20 Merck Patent Gmbh Substituted azoxy benzene compounds
DE2024269A1 (en) * 1970-05-19 1971-12-02 Merck Patent Gmbh Nematic mixtures - of low melting point, used in electronics
US3853785A (en) * 1971-10-14 1974-12-10 Univ Temple Stable liquid crystal mixtures including anil-type nematic compounds

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4134888A (en) * 1975-12-22 1979-01-16 Rca Corporation Cholesteryl carbonates and carbamates of azo dyes
US4199503A (en) * 1977-10-12 1980-04-22 Basf Aktiengesellschaft Phenylazophenyloxytriazolyl compounds
US5314997A (en) * 1991-07-11 1994-05-24 Ricoh Company, Ltd. Optically active azo compound, producing method thereof, and liquid crystal composition containing said compound
US9242869B2 (en) 1997-09-19 2016-01-26 Opko Ireland Global Holdings, Ltd. Metal compounds mixed or sulphated, as phosphate binders
US7799351B2 (en) 1997-09-19 2010-09-21 Ineos Healthcare Limited Metal compounds, mixed or sulphated, as phosphate binders
US20110014301A1 (en) * 1997-09-19 2011-01-20 Ineos Healthcare Limited Metal compounds, mixed or sulphated, as phosphate binders
US8568792B2 (en) 1997-09-19 2013-10-29 Cytochroma Development Inc. Metal compounds, mixed or sulphated, as phosphate binders
US20040105896A1 (en) * 1997-09-19 2004-06-03 Crosfield Limited Metal compunds, mixed or sulphated, as phosphate binders
US9907816B2 (en) 2006-01-31 2018-03-06 Opko Ireland Global Holdings, Ltd. Water-insoluble, iron-containing mixed metal, granular material
US20090317459A1 (en) * 2006-01-31 2009-12-24 Ineos Healthcare Limited Material
US9168270B2 (en) 2006-01-31 2015-10-27 Opko Ireland Global Holdings, Ltd. Water-insoluble, iron-containing mixed metal, granular material
US20100203152A1 (en) * 2007-07-27 2010-08-12 Ineos Healthcare Kimited Mixed metal compounds used as antacids
US10201501B2 (en) 2007-07-27 2019-02-12 Opko Ireland Global Holdings, Ltd. Mixed metal compounds used as antacids
US20100215770A1 (en) * 2007-10-16 2010-08-26 Maurice Sydney Newton Mixed metal compounds for treatment of hyperphosphataemia
US10155040B2 (en) 2007-10-16 2018-12-18 Opko Ireland Global Holdings, Ltd. Mixed metal compounds for treatment of hyperphosphataemia
US9066917B2 (en) 2009-08-03 2015-06-30 Cytochroma Development Inc. Mixed metal compound
US9314481B2 (en) 2009-08-03 2016-04-19 Opko Ireland Global Holdings, Ltd. Method
US9566302B2 (en) 2010-02-04 2017-02-14 Opko Ireland Global Holdings, Ltd. Composition comprising mixed metal compounds and xanthan gum

Also Published As

Publication number Publication date
DE2456804A1 (de) 1975-06-19
AU7634574A (en) 1976-06-17
JPS598270B2 (ja) 1984-02-23
JPS55147583A (en) 1980-11-17
JPS6121507B2 (enrdf_load_stackoverflow) 1986-05-27
FR2254556B1 (enrdf_load_stackoverflow) 1978-12-01
FR2254556A1 (enrdf_load_stackoverflow) 1975-07-11
JPS5092280A (enrdf_load_stackoverflow) 1975-07-23
IT1027046B (it) 1978-11-20
GB1435269A (en) 1976-05-12
BE823358A (fr) 1975-06-13
NL7317074A (nl) 1975-06-17
SE416199B (sv) 1980-12-08
CH612415A5 (enrdf_load_stackoverflow) 1979-07-31
NL174720C (nl) 1984-08-01
SE7415417L (enrdf_load_stackoverflow) 1975-06-16
NL174720B (nl) 1984-03-01
DE2456804C2 (de) 1982-02-25

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